Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide → HCID 10231894, compound

HRID 720925Notes

Reaction equation

HRID 720925 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:29]1[CH2:31][C@@H:30]1[CH2:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[N:40]=[CH:39][CH:38]=[CH:37]2>C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:31][C@@H:30]([OH:29])[CH2:32][O:33][C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[N:40]=[CH:39][CH:38]=[CH:37]4)[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12020260Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideHCID 59885584HCID 59885584, compound

Product 1

HCID 10231894HCID 10231894, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (4) (100.0 mg; 0.264 mmol) is dissolved in ethanol (10 mL) at ambient temperature. (R)-6-Oxiranylmethoxy-quinoline (89) (53.0 mg; 0.264 mmol) is added, then the mixture is refluxed for 17 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (70%→90% ethyl acetate in hexanes, then 50%→70% acetone in hexanes) affording the desired product (50 mg) as a white solid. ESMS:MH+ 580.4.

Workup

  1. temperaturethe mixture is refluxed for 17 hours
  2. concentrationthe solution is concentrated in vacuo at 40° C
  3. customThe residue is purified via silica gel chromatography with gradient elution (70%→90% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a80be26f87cd4524a21ec92a204cc402
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

Loading…